How the Devil Totally Hooked Up the Winchesters
by ugmohoe
Summary: AU. Sam goes to hell instead of Dean. Lucifer plays matchmaker, Sam comes out of the closet, Dean searches desperately for his beloved, and Sam is told to go get his man. .Wincest.
1. Chapter 1

**Ohmygosh guyz, my first multi-chaptered story! Please read and review and critique and love because I love youuuu 3**

**Title: How the Devil Totally Hooked Up the Winchesters**

**Rating: T (language, nongraphic wincest)**

**Spoilers: Set season 3-ish, so spoilers all through there. I completely disregard the existence of anything in season 4 or 5, because that is not the Lucifer of MY dreams. Consider this an AU.**

**Summary: AU. Sam goes to hell instead of Dean. Lucifer plays matchmaker, Sam comes out of the closet, Dean searches desperately for his beloved, and Sam is told to go get his man. **

* * *

On February twenty-second, Sam goes to hell.

The idea had been simple enough. It included a crossroads, Ruby admitting her ultimate bitchiness, and a few things Sam wasn't too proud of. Dean didn't know, and Sam didn't tell him. He'd wanted to, seen the opportunity a million zillion times, but then Dean would say some bullshit about how he'd do _anything_ to save his little brother, and how Sam had to _promise _not to use those freaky powers to get him out of it, you know, guilt-trips like that. Sam was a chickenshit till the bitter end, leaving Dean a note where he'd find it, and trotting off to face his destiny. Or whatever.

So, Sam went to see this demon chick, who mentioned Lucifer's interest in Sam only briefly after administering the shot. "What now?" Sam had asked, feeling very, very stupid. The demon had smiled, eyes all black and ominous as she said

"In good time, Sam Winchester. In good time."

Which, 'said' isn't a good adjective at all, Sam heard it as much more a hiss, like popping open a can of coke, only the coke had bad intentions.

The poison kicks in pretty quick, and not painfully. He'd gotten the luxury of choosing where and how the whole death thing was gonna go down. Apparently, hellhounds were a last resort Lucifer was not partial to. He'd chosen a little empty road, and told Dean where to find him in the letter. Sam was getting out of hell, and he didn't want a shot open, stabbed, burned, decaying body to chill in. A particular image of maggots popping out of his eyes always seemed to burrow its way into that train of thought.

Sam is not a liar. Not a big one, at least. The idea of dying scares him a little. From the time that he was dead, he doesn't remember much. He thinks it was pretty much black, and he thinks there were some discussions about where to put him, like some sort of ADHD kid who refuses to stop doing the vocabulary quizzes in crayons. Before anything serious had happened, Dean had pulled him back out. That wouldn't be happening this time. Sam knew just where he was headed, and if he wanted out, it was going to be his own doing. It's all explained in the letter.

He actually researched the poison for weeks. Dean had rested his chin on Sam's knee, peeking at the screen.

"Dude. I'm telling you, it's not anything human killing those girls." He said.

Sam ignored the amazing little horny-lightning shooting up his spine because Dean was so close to his crotch, and sighed in very put upon way.

"We can't just go in guns ablaze, Dean. Just let me do what I'm good at."

"Not getting laid?"

"Not all of us can be man whores."

Dean had stiffened and rolled away from Sam, moving over to his own bed. Sam immediately felt a little guilty.

"Did you know man whore is actually a synonym for awesome?" He said, trying his best to channel apology. Dean smirked, and stretched his entire body.

"Like I said. You need to get laid."

* * *

Sam goes down in a crumpled heap, not some graceful falling back and landing sprawled out and sexy. Oh no. His mouth is spitting out hunks of dirt when he dies. He may have shit his pants.

_Dean is going to give me hell for this._

Sam will say was his last thought before dying. But that isn't true. Sam was thinking of Dean, of course, and he was thinking

_Totally worth it. _


	2. Chapter 2

_Hi there! So, I wrote another chapter. I hope you like it, or have something say about it, or, like, want to crush my fragile, blossoming writer-heart, because all comments are good comments. _

* * *

The first thing Dean did when he woke up is check on Sam, who was, strangely, not in his proper place.

"Goddammit," Dean said, punching the pillow. "Little bitch better not use all the hot water." Only then Dean realized the water wasn't running. Which was, you know, not completely unusual considering how long Sam takes primping or jacking off or whatever. Dean rolled over and drifted back off to sleep. The clock said 8:37.

* * *

Dean woke up again at 9:23. He really needed to pee. Sam was still in the bathroom. His brother was ridiculous.

Dean rolled out of bed and stumbled over to the bathroom door.

"Hate to be the one to tell you, Princess, but ugly isn't something you can wish away." He yelled.

Sam was quiet behind the door. Dean could just picture him sighing and pushing around his terrible hair. Dean pounded on the door twice, and then decided to wait his brother out, sitting outside the door, slamming his legs into it repeatedly. Ten minutes later, Dean had had enough. He grabbed the single wire hanger in the motels tiny closet, and stomped back the door.

"One more minute, Sammy, and I swear to god, I'm coming in."

Dean grumbled, and reached to pick to the lock. The handle turned easily in his palm.

"Shit." The bathroom was cold and empty. The shower was completely dry. Sam hadn't been there all morning.

"Bitch better be picking me up a goddamn glazed donut."

Dean cursed again and headed toward the Impala, pushing back the panic with slow, in-through-your-nose, breaths. He pulled out his phone and dialed Sam, just as he was pulling out of the parking lot. It went to straight to voice mail.

"Godfuckingdammit."

Dean was calling Sam again when he saw the note, written on a pink post it Sam had somehow acquired. Dean couldn't think of anything very clever, which should say something. There was an address, and a shitload more, but Dean wasn't really concerned with that.

Sam ended being laid across a crossroads, looking unfairly hot, and also very much dead. The hair was pushed back from his face, his hands folded (um, so, actually, this was definitely a finer point of a certain someone's Master Plan), and his whole body smelling vaguely of vanilla. Dean knew because he sobbed into Sam's button-down shirt, for like, several hours. Which is embarrassing.

Eventually Dean got up enough strength to go and vomit in the nearby grass. He also picked up Sam and put him the back of the car. He screamed, he cried some more, and only then did he get it together enough to summon a demon.

Her name was Karen, and she was surprisingly kind about the whole thing. In that, you know, demon-y sort of way.

"I'm surprised you haven't blown your brains out yet." She said, popping a loud, obnoxious bubble.

"I'm not really in the mood for small talk, sweetheart." Dean said, voice barely shaking, "Now tell me what the _fuck _you did with Sam."

Karen rolled her eyes, and plopped down in the gravel road, crossing her legs.

"Relax, babe. I come bearing gifts."

"Let's just get this over with." Dean said, staring down at her, "My soul for Sam's. You get who you ordered in the first place."

"Whoa now, that's some heavy stuff your asking me to do. I just want to have a chit-chat, Deany-Pie."

"I want you to do this quick clean. Right now, take me, give Sammy back. It's a fair trade."

"God, does anything get through that stupid skull of yours?" Said Karen, "I'm not here to make a deal. I'm here on orders, and we've got some things to discuss. Now sit yourself down. This is going to take awhile."

* * *

Karen was very supportive when Dean started crying. "Fucking pussy." She said, digging out a tissue.

"I hope you know how much I hate doing this." She said.

"Demons lie." Dean said, "I don't believe you."

Karen sighed. "You want to try a million demons, they're all gonna tell you the same thing. Sammy is getting out of hell when he finds himself a way out. You're not getting in, it's impossible, and I'm sorry. This has to suck. But Lucifer wanted your little boyfriend-"

"Brother."

"Yeah, sure. He wanted Sam specifically, and no one really knows why. I'm just supposed to be the bearer of bad news. Even though, there's like, a note and everything. I guess everyone knew you'd be too stupid to actually read it."

"There's a way." Dean said, turning to get back in the Impala.

"Um, no. There really isn't. I'm not trying to be all metaphoric about the journey just being difficult. You physically cannot get into hell. There are Dean-Winchester alarms rigged up to make sure you keep your cute little self on earth. Getting into hell truly is not an option you possess."

"I'm calling Bobby." Dean said, whipping out his phone.

"Oh mother of god."

* * *

Bobby, as it turned out, was as helpful as ever. He promised Dean he would do some research, and hung up. Karen looked at Dean expectantly.

"Bobby's doing some research." Dean said.

"Okay. You let me know when he finds something, in, oh, I don't know, never."

"Funny."

Dean got back in the car, and slammed the door behind him.

"Where you going?" Karen asked as Dean started the car.

"I'm finding Sam a way out of hell." Dean said, pointedly ignoring his dead brother's reflection in the mirror, and the empty passenger seat, and the huge, gory hunk of him that was sliced out of his ribcage, and stung like a mother. This is, of course, symbolic.

"God speed on your pointless quest, Dean Winchester." Said Karen, giving him a little wave.

Dean focused on not crying anymore.


	3. Chapter 3

_Hello darling readers! I'm back with another installment :) I hope you enjoy. I spend quite a bit of time on writing these things, so I think the bestest thing you could ever do is write me a review. I'd really appreciate it. It would probably make my life. And I lead a pretty exciting life._

* * *

Hell, for the first couple of weeks, isn't all that wonderful. Sam dies in countless, terrible, painful ways, and then he wakes up, and he's in his cell, healed right back up. He woke up, originally, tied spread eagle to a round, wooden board. For two days, demons had come and gone, throwing more sharp objects at him than Sam knew existed. They had terrible aim. In one particularly memorable death, Sam had been subjected to a cannibalistic young woman who'd worked her way up to a mid-level Torturer. She had terrible, frizzy hair. There was no excuse, as hell was surprisingly temperate. He didn't like her very much.

It was weird though. Sam had expected something a little more, well, just more. He'd thought for sure that there were demons with something against him down here, just waiting for his arrival. For all the weeks of torture, he hadn't been recognized once. He wasn't even on a very strict T-schedule. He got tortured once a day, maybe twice, and in between he was just slung in a moderately unattractive cell. It left some time for thinking. Mostly about Dean.

Hell was, at times, incredibly dull. Sam had spent days counting the ceiling tiles, because, yes, his cell looked somewhat like an empty office space. The number of tiles changed every day, Sam noted, if he wasn't going crazy. The worst part about hell wasn't really the torture, it was the constant waiting. Sam had anxiousness, and a constant, gnawing hunger making his body achy and nervous and he'd start drifting off into thoughts, and right back to Dean.

Dean who he was deeply, deeply concerned about but tried not to focus on. Dean-thoughts hurt deep and fresh. He knew how his brother was reacting. He was pissed, and hurt, and crazy because by now he'd figured out he couldn't _do _anything. But he hadn't given up.

Sam was selfish, he wouldn't deny it. He thought of Dean and he missed him so fucking much, and he thought of Dean's face and his laugh. He'd imagine Dean's voice, deep and rough, speaking to him for hours, and he'd smile and whisper "Yeah, Dean, I know." So, Sam was basically kind of lame, and crazy, but he still thought it was worth it, because at least Dean was alive.

Sam's cycle of crazy-torture-counting ceiling-crazy-talktoDean-torture-crazy was broken on the fourth week by Karen. She unlocked the door to his cell with a bowl of Caesar salad and cheesecake. He peeked up from his spot laying on the floor and gave a tiny wave. "So, what, it's poisoned? Weak." She immediately liked him.

As it turned out, the food was a bit of a piece offering from Lucifer.

"He feels just awful about you getting so horribly misplaced. It's a big system, you know. It's easy to lose one very important soul."

"No worries. This definitely makes up for all the meaningless, senseless torture." Sam said, chomping on a piece of lettuce. "But since he's so interested, I would like to talk with him."

Karen smiled indulgently, "Oh, Sam, you silly boy. Lucifer doesn't see _anyone _these days. He just doesn't have the time. Consider me your personal messenger."

Sam scoffed, "Right. I'm going to trust you to deliver my exact words to Lucifer, without screwing me over whatsoever."

"If I had something against you, I wouldn't be chosen to deliver the apology-lunch."

She had a point, Sam figured.

"Who says you wouldn't do it just for fun?" He asked, raising one eyebrow in a very intimidating (he thought) stare.

"Oh, puh-lease. Do you think I'm fucking retarded?"

"Using the word retarded is offensive." Sam said automatically. Karen snorted.

"Stripping the skin off a fifteen men isn't super great either, but that's what I did this morning."

Sam was brought back instantly to exactly who he was talking to. He glared. "I want to deliver a message to Lucifer. I'd like a pen, and paper, and an envelope, or else he isn't getting anything from me."

"Who says he wants something from you?"

"You really should watch your employees a little more carefully." Sam said, Karen's eyes narrowed.

"Listen up, Sam Winchester. The devil brought you down here as a little bit of amusement. He doesn't _need_ anything from you. I suggest cooperating, so the guy doesn't change his mind. He's known for that. The mood swings. And I can swear to you, the first thing he'll do when he snaps, is send half of hell after that brother of yours." And that, Karen thought in retrospect, was probably not a good move.

In half a second Sam had Karen flying across the cell, pinned to the wall, his expression sharp and dangerous. Like, she could probably touch his face and get her finger fucking sliced off. Seriously. He stalked forward, the pressure holding Karen increasing with every step. She felt her ribs cracking. Which, in hell, is not a petty as it may be on Earth.

"I've figured a couple tricks out while Lucifer left me rotting in this cell. Turns out, my powers work just fine down here. Now. I'm going to ask you again. Pen. Paper. Motherfucking envelope."

Karen nodded hurriedly. Maybe this wouldn't be as hard as she thought.


End file.
